ID: ALA2040589

Max Phase: Preclinical

Molecular Formula: C28H24O5

Molecular Weight: 440.50

Molecule Type: Small molecule

Representations

Synonyms (1): Marchantin A
Synonyms from Alternative Forms(1):

Canonical SMILES:  Oc1cc2cc(c1O)Oc1ccc(cc1)CCc1cccc(O)c1Oc1cccc(c1)CC2

Standard InChI:  InChI=1S/C28H24O5/c29-24-6-2-4-21-12-9-18-10-13-22(14-11-18)32-26-17-20(16-25(30)27(26)31)8-7-19-3-1-5-23(15-19)33-28(21)24/h1-6,10-11,13-17,29-31H,7-9,12H2

Standard InChI Key:  LLMFFOXSSQHNFR-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 440.50

Molecular Weight (Monoisotopic): 440.1624

AlogP: 6.27

#Rotatable Bonds: 0

Polar Surface Area: 79.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.40

CX Basic pKa:

CX LogP: 7.16

CX LogD: 7.12

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: 2.20

References

1. Harinantenaina L, Quang DN, Takeshi N, Hashimoto T, Kohchi C, Soma G, Asakawa Y..  (2005)  Bis(bibenzyls) from liverworts inhibit lipopolysaccharide-induced inducible NOS in RAW 264.7 cells: a study of structure-activity relationships and molecular mechanism.,  68  (12): [PMID:16378374] [10.1021/np0502589]

2. Morita H, Zaima K, Koga I, Saito A, Tamamoto H, Okazaki H, Kaneda T, Hashimoto T, Asakawa Y..  (2011)  Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.,  19  (13): [PMID:21652215] [10.1016/j.bmc.2011.05.019]

3. Iwai Y, Murakami K, Gomi Y, Hashimoto T, Asakawa Y, Okuno Y, Ishikawa T, Hatakeyama D, Echigo N, Kuzuhara T..  (2011)  Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.,  6  (5): [PMID:21625478] [10.1371/journal.pone.0019825]

4. Asakawa Y, Ludwiczuk A, Novakovic M, Bukvicki D, Anchang KY..  (2022)  Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity.,  85  (3.0): [PMID:34783552] [10.1021/acs.jnatprod.1c00302]

5. Asakawa Y, Ludwiczuk A..  (2018)  Chemical Constituents of Bryophytes: Structures and Biological Activity.,  81  (3): [PMID:29019405] [10.1021/acs.jnatprod.6b01046]

Source

Source(1):

• Scientific Literature